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496 Beach Street, Ashland
$845,000
5 Beds ⋅ 6 Baths ⋅ 220230213 MLS
Gorgeously renovated Victorian blends historic charm with modern luxury in the heart of Ashland. R2 zoning offers versatile living: A gracious private residence, a home with Airbnb units, or a B&B with owner-occupied quarters. Once the beloved Midsummer Night's Dream B&B, it's now a private home with 2 vacation rentals in a stunning detached annex. The main house (2375 SF) features hardwood floors, a lovely living room with fireplace, parlor/game room, formal dining room, chef's kitchen, laundry room, & small office. Three luxurious suites are in the main home, with two more in the annex (1092 SF), each with a fireplace, spa bath, shower & a private deck. Expansive lush lawn areas with mature flowering trees & mountain views, creates a peaceful & picturesque setting. Unbeatable location near theaters, dining, & the magic that is Ashland. Off street parking. Most furnishings included. An exceptional opportunity for a family home, extended family living or income. Request information.

496 Beach Street, Ashland

322 N 3rd Street, Central Point
$639,000
4 Beds ⋅ 3 Baths ⋅ 220228927 MLS
Offering flexible living and established income history, this updated Victorian farmhouse pairs 1895 character with real modern comfort. On a fenced 0.35-acre corner lot, the 4-bedroom home features 9.5-foot ceilings, abundant natural light, a spacious main-level primary suite with remodeled bath and radiant heated floors, a remodeled laundry room, large kitchen and a cozy wood stove. Out back, a private retreat: a 400 sq. ft. covered outdoor kitchen and entertaining area, hot tub, gardens, orchard and mature fruit trees. The detached two-car garage also houses the 420 sq. ft. Bee Well Garden Guesthouse ADU with its own kitchen and bath -- ideal for extended family, guests or rental use, with an established eight-year Airbnb and VRBO history and documented revenue available on request. 24-panel solar system. Central Point School District, blocks from downtown dining, shopping, and minutes from Rogue Valley wine country.

322 N 3rd Street, Central Point

49 California Street, Ashland
$317,000
2 Beds ⋅ 2 Baths ⋅ 220229021 MLS
Charming 2004 built Victorian-style townhouse offering the perfect blend of classic character and modern convenience. This inviting end unit features 2 bedrooms and 1½ baths, with wood floors extending through the entry and living room. The comfortable floor plan offers a warm, welcoming living space with plenty of natural light and easy flow. Step outside to the back deck, ideal for relaxing, enjoying your morning coffee, or entertaining friends. As an end unit, this home offers added privacy and a desirable setting. Conveniently located near schools, shopping, dining, and everyday amenities, this delightful townhouse is a wonderful opportunity for comfortable, low-maintenance living with plenty of charm. Note, all tenant possessions have been removed from all photos.

49 California Street, Ashland

640 Carriage Lane, Jacksonville
$790,000
4 Beds ⋅ 3 Baths ⋅ 220228879 MLS
Charming Victorian-style home in quiet, desirable neighborhood in Historic Jacksonville. Beautifully landscaped .19 acre, 4 bdrm, 2.5 bath, 2,259 sf home. Enjoy cooking in the large kitchen w/ island, granite counters, stainless steel Bosch appliances, soft-close cabinetry w/ lots of natural light. Kitchen is open to the family room w/ gas fireplace and sliding glass doors leading to the private, landscaped backyard w/ built-in firepit, gazebo, greenhouse and garden. Great room also has a gas fireplace and opens to a separate dining room area. Relax on the covered front porch and enjoy the manicured yard and mountain views. Awake to views from the primary bdrm w/ walk-in closet, lg vanity w/ dbl sinks, step-in shower, and enclosed toilet. Extra wide garage suitable for a sm. workshop & storage areas. Neighborhood is near walking trails, close to downtown and vineyards.

640 Carriage Lane, Jacksonville

425 S Oakdale Avenue, Medford
$375,000
4 Beds ⋅ 2 Baths ⋅ 220228829 MLS
Step into the charm of this remodeled 4 bedroom, 2 bathroom home built in 1910 and recently updated! Set nicely back from the street, the entry welcomes you with a classic front porch and generous entry. The large living room and spacious dining room feature tall ceilings, in line with the early 20th century design. The kitchen has been remodeled with new butcher block counters and invites tons of natural light into the space. A laundry room and full bathroom, along with an office or 4th bedroom are featured on the main level. Upstairs you'll find the well preserved wooden staircase along with three additional bedrooms and another full bath. Beautifully restored hardwood floors remain, along with new simulated wood floors and carpet. The home has a newer roof and was painted inside and out - it's ready for the next owners to love!

425 S Oakdale Avenue, Medford

1098 Nick Young Road, Eagle Point
$3,700,000
4 Beds ⋅ 1 Baths ⋅ 220228293 MLS
Rare opportunity to own 127 acres in Eagle Point with approximately 80 irrigated acres from Little Butte Creek. This versatile property features an established vineyard with 10 varietals, an extensively remodeled farmhouse, brand-new office with modern accommodations including a restroom and kitchen, two wells, and a fully equipped winery. The winery retains the equipment used during years of wine production from 2005-2019, making this an ideal opportunity for someone looking to pursue or revive a vineyard and wine operation. The irrigated pasture has been carefully maintained and is fully set up for irrigation, making it ideal for cattle, hay production, or other agricultural uses. Solar panels provide approximately $20,000 in annual income, increasing toward $25,000. Combining irrigated acreage, vineyard, winery, remodeled improvements, water resources & solar income, 1098 Nick Young Rd offers a rare opportunity to create a distinctive Southern Oregon agricultural estate

1098 Nick Young Road, Eagle Point

1098 Nick Young Road, Eagle Point
$3,700,000
4 Beds ⋅ 1 Baths ⋅ 220228292 MLS
Rare opportunity to own 127 acres in Eagle Point with approximately 80 irrigated acres from Little Butte Creek. This versatile property features an established vineyard with 10 varietals, an extensively remodeled farmhouse, brand-new office with modern accommodations including a restroom and kitchen, two wells, and a fully equipped winery. The winery retains the equipment used during years of wine production from 2005-2019, making this an ideal opportunity for someone looking to pursue or revive a vineyard and wine operation. The irrigated pasture has been carefully maintained and is fully set up for irrigation, making it ideal for cattle, hay production, or other agricultural uses. Solar panels provide approximately $20,000 in annual income, increasing toward $25,000. Combining irrigated acreage, vineyard, winery, remodeled improvements, water resources & solar income, 1098 Nick Young Rd offers a rare opportunity to create a distinctive Southern Oregon agricultural estate

1098 Nick Young Road, Eagle Point

Medford
$440,000
5 Beds ⋅ 4 Baths ⋅ 220226637 MLS
This turn of the century house is conveniently located in down town Medford. There are many possible investment opportunities. 5 rooms and 4 full bathrooms. There are two room ensuites upstairs and one room ensuite down stairs with French doors. This could be a nice office area. A nice size living room featuring a large wood fireplace. At the entrance is a walk-in closet space or another small office with a front window. Original hardwood floors, a separate large dining area with built in cupboards and drawers. kitchen has a large walk-in food pantry, dishwasher and an island. The mornings are perfect to sit out on the front covered porch which has a ceiling fan to enjoy the sunrise. At the back of the house there are 4 sheds, a small covered deck. There is a sprinkler system to water of the fruit trees. The Fig tree is a great shade area. Parking area is near the back.

Medford

508 N Main Street, Ashland
$489,000
3 Beds ⋅ 2 Baths ⋅ 220225550 MLS
DRAMATIC PRICE REDUCTION TO $489,000. Looking for a home in Ashland that offers more than just a place to live? 508 N Main Street offers a unique opportunity to own a distinctive Victorian property with two separate living spaces. Currently arranged as two 1-bedroom, 1-bath living areas, this versatile property offers the opportunity to live in one space while exploring rental income from the other, subject to applicable regulations. It could also be ideal for multigenerational living, guests, or a dedicated home office. Enjoy mountain and territorial views, charming patio and garden areas, off-street parking, additional storage, and a dry sauna-- all less than a mile from downtown Ashland. REDUCED By $55,900. If you've been waiting for an opportunity to own property in Ashland with flexible living options and potential income-producing space, this is one to explore.

508 N Main Street, Ashland

541 Fairview Street, Ashland
$996,000
5 Beds ⋅ 3 Baths ⋅ 220225227 MLS
Beautifully restored 1908 classic home located on a rare R2 zoned double lot just blocks from downtown Ashland's theatres, restaurants, galleries, and parks. MAIN RESIDENCE Featuring 3 bedrooms and 2 full baths, interior highlights include original fir floors, high ceilings, designer lighting, updated kitchen, pantry and abundant natural light throughout. Flexible layout supports guest space, office, or extended living arrangements. LOWER LEVEL Remodeled with separate entrance, kitchen, bedroom and full bathroom offering independent living space. Foundation of main home was updated in 1997 with central heat, air, electrical and plumbing systems. DETACHED COTTAGE Separate remodeled cottage with bedroom and bath ideal for additional flexible living needs, guest suite, or office. OUTDOOR FEATURES Mature landscaping with fenced yard, irrigation, water feature, dry sauna, spa, storage shed, and ample off street parking. ADDITIONAL HIGHLIGHTS R2 zoning ideal for income producing living.

541 Fairview Street, Ashland

4303 Tami Lane, Central Point
$1,695,000
4 Beds ⋅ 5 Baths ⋅ 220225149 MLS
Looking for a 2 FAMILY SET UP with incredible views? This exceptional property's breathtaking panoramic views sweeping from Eagle Point to Ashland offers Victorian charm paired with modern comfort. Just under 5 Acres and almost 4300 sq ft, this 4 bedroom 5 bath residence, features two complete living quarters, each with its own full kitchen, private entrance, and laundry area, making it ideal for multigenerational living, family, guests, or rental income potential. The upper level is enhanced by balconies on each side of the home providing the perfect place to enjoy morning coffee and evening nights. Also featuring a Stiltz Elevator for convenient access to upper level. Main level of the home has a great floor plan with space for everyone inside and out with a covered porch. The four-car garage provides abundant space for vehicles, toys and storage. Ideally located just minutes from the historic town of Jacksonville, wineries, and shopping, this home is truly incredibe.

4303 Tami Lane, Central Point

75 Wimer Street, Ashland
$759,000
5 Beds ⋅ 6 Baths ⋅ 220221349 MLS
71, 73 and 75 Wimer. Gorgeous updated including plumbing and electric vintage home w/charm remaining a few blocks to downtown Ashland. The main home has 3 bedrooms (2 with ensuite baths) the 3rd bedroom has an ensuite 1/2 bath. Formal living and dining and eat in large kitchen w/breakfast bar & nook. Granite countertops. Wood floors on main level & carpet on stairs & bdrms. The woodwork door trim is beautiful & probably original. Newer deck & A/C unit. Detached building (71 and 73 Wimer) are one level studio units with kitchens & baths. 73 Wimer has private deck. Main house is rented for $2375.00 p/month & tenant pays utilities except water. Studios have been rented for $1250.00 & $1350.00 per month with utilities included & they have a separate shared laundry facility. Unique property for owner occupied or income producing. Circular driveway for main home & 2 parking spaces in front for studios. Has been traveler accomodations in the past. Buyer to do own due diligence on u

75 Wimer Street, Ashland

1320 E Main Street, Medford
$499,480
5 Beds ⋅ 2 Baths ⋅ 220213933 MLS
A stunning two-story home one of East Medford's earliest homes built in 1890 and a rare piece of Southern Oregon history. All furniture, appliances & decor included in sale. Meticulously maintained & brimming with timeless character, house is 2,348 sq ft + basement is 480 sq ft. this treasure sits on a generous 0.28 acre lot with stunning, mature landscaping that creates a private oasis of tranquility. A private garden in the back of the home that leads to a screened in porch. Inside the home Soaring 9-foot ceilings, elegant crown molding, classic wainscoting and gleaming original hardwood floors showcase the craftsmanship throughout the spacious layout. Downstairs a beautiful updated kitchen with marble counters, Bluestar gas range, pantry. Dinning room w/ built in cabinets. Living room has a fireplace and 1 bedroom downstairs & half bath & 4 bedrooms upstairs with a full bath. Updated HVAC & ,new sewer lines. See Video

1320 E Main Street, Medford

451 N Main Street, Ashland
$1,249,000
8 Beds ⋅ 9 Baths ⋅ 220212846 MLS
Just blocks from downtown, this historic gem blends charm and flexibility. Original fir floors, built-ins, high ceilings, and abundant natural light pair with modern updates. Enjoy the welcoming lawn, pollinator garden, and large covered front porch. The main level offers spacious living and dining areas, kitchen, half bath, and generous entry spaces. A 1-bedroom apartment with interior and private exterior access--includes a kitchen, laundry and full bathroom--a separate additional en-suite bedroom with exterior entry adds versatility. Upstairs are four lovely en-suite bedrooms, one with a balcony, all with updated Renewal by Andersen windows and balcony door. A detached 704 sq ft, 2 bedroom, 1.5 bath, single level cottage with its own address and electric meter provides added flexibility or income potential. With six paved off-street parking spaces, sheds, on-street parking, and alley access, this property offers exceptional possibilities for multi-generational living or investors.

451 N Main Street, Ashland

The content relating to real estate for sale on this site comes in part from the IDX program of the RMLS of Portland, Oregon. Real Estate listings held by brokerage firms other than this firm are marked with the RMLS logo, and detailed information about these properties include the name of the listing's broker. Listing content is copyright © 2026 RMLS of Portland, Oregon. All information provided is deemed reliable but is not guaranteed and should be independently verified. This content last updated on . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

The data relating to real estate for sale on this web site comes in part from the Internet Data Display (IDX) of the Southern Oregon Multiple Listing Service. Real estate listings held by brokerage firms other than our company are marked with the IDX logo and detailed information about them includes the name of the listing brokers. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information subject to change and should be independently verified. Listing content is copyright © 2018 SOMLS, Medford, Oregon. Last updated:

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